An efficient catalyst- and solvent-free method for the synthesis of medicinally important dihydropyrano[2,3-c]pyrazole derivatives using ball milling technique
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  • 作者:Mohammad G. Dekamin ; Mohammad Alikhani…
  • 关键词:Catalyst ; free conditions ; Solvent ; free conditions ; Ball milling technique ; Green chemistry ; Multicomponent reactions (MCRs) ; Dihydropyrano[2 ; 3 ; c]pyrazole scaffold
  • 刊名:Journal of the Iranian Chemical Society
  • 出版年:2016
  • 出版时间:March 2016
  • 年:2016
  • 卷:13
  • 期:3
  • 页码:591-596
  • 全文大小:530 KB
  • 参考文献:1.B.H. Rotstein, S. Zaretsky, V. Rai, A.K. Yudin, Chem. Rev. 114, 832 (2014)CrossRef
    2.M.M. Heravi, S. Moghimi, J. Iran. Chem. Soc. 8, 306 (2011)CrossRef
    3.H. Eshghi, M. Rahimizadeh, F. Eshkil, M. Hosseini, M. Bakavoli, M. Sanei-Ahmadabad, J. Iran. Chem. Soc. 11, 685 (2014)CrossRef
    4.A.R. Moosavi-Zare, M.A. Zolfigol, O. Khaledian, V. Khakyzadeh, M.D. Farahani, M.H. Beyzavi, H.G. Kruger, Chem. Eng. J. 248, 122 (2014)CrossRef
    5.P.B. Oshiro, P.S. Lima, M.L. de Menezes, L.C. da Silva-Filho, Tetrahedron Lett. 56, 4476 (2015)CrossRef
    6.M.A. Terzidis, V.G. Tsiaras, N.M. Drosos, P.M. Kasapidou, J. Stephanidou-Stephanatou, C.A. Tsoleridis, G. Buth, G.E. Kostakis, Tetrahedron Lett. 55, 5601 (2014)CrossRef
    7.L.G. Voskressensky, Chem. Heterocycl. Comp. 48, 535 (2012)CrossRef
    8.M.G. Dekamin, M. Eslami, Green Chem. 16, 4914 (2014)CrossRef
    9.M.G. Dekamin, M. Eslami, A. Maleki, Tetrahedron 69, 1074 (2013)CrossRef
    10.M.G. Dekamin, M. Azimoshan, L. Ramezani, Green Chem. 15, 811 (2013)CrossRef
    11.S. Shaaban, B. Abdel-Wahab, Mol. Divers. (2015). doi:10.​1007/​s11030-015-9602-6
    12.Y. Huang, A. Dömling, Mol. Divers. 15, 3 (2011)CrossRef
    13.C.C. Musonda, D. Taylor, J. Lehman, J. Gut, P.J. Rosenthal, K. Chibale, Bioorg. Med. Chem. Lett. 14, 3901 (2004)CrossRef
    14.N. Sudhapriya, P.T. Perumal, C. Balachandran, S. Ignacimuthu, M. Sangeetha, M. Doble, Eur. J. Med. Chem. 83, 190 (2014)CrossRef
    15.G. Mohammadi Ziarani, S. Faramarzi, N. Lashgari, A. Badiei, J. Iran Chem. Soc. 11, 701 (2014)CrossRef
    16.O. Hosseinchi Qareaghaj, S. Mashkouri, M.R. Naimi-Jamal, G. Kaupp, RSC Adv. 4, 48191 (2014)CrossRef
    17.G. Kaupp, Cryst. Eng. Comm. 8, 794 (2006)CrossRef
    18.G. Kaupp, Cryst. Eng. Comm. 13, 3108 (2011)CrossRef
    19.J. Mokhtari, M.R. Naimi-Jamal, H. Hamzeali, M.G. Dekamin, G. Kaupp, Chemsuschem 2, 248 (2009)CrossRef
    20.M.R. Naimi-Jamal, J. Mokhtari, M.G. Dekamin, G. Kaupp, Eur. J. Org. Chem. 2009, 3567 (2009)CrossRef
    21.A. Stolle, T. Szuppa, S.E.S. Leonhardt, B. Ondruschka, Chem. Soc. Rev. 40, 2317 (2011)CrossRef
    22.S. Mashkouri, M.R. Naimi-Jamal, Molecules 14, 474 (2009)CrossRef
    23.S.K. Khetan, T.J. Collins, Chem. Rev. 107, 2319 (2007)CrossRef
    24.M. Li, B.-X. Zhao, Eur. J. Med. Chem. 85, 311 (2014)CrossRef
    25.S.R. Mandha, S. Siliveri, M. Alla, V.R. Bommena, M.R. Bommineni, S. Balasubramanian, Bioorg. Med. Chem. Lett. 22, 5272 (2012)CrossRef
    26.D. Das, R. Banerjee, J. Chem. Pharm. Res. 6, 108 (2014)
    27.J.R. Zgoda, J.R. Porter, Pharm. Biol. 39, 221 (2001)CrossRef
    28.Y. Zou, Y. Hu, H. Liu, D. Shi, ACS. Comb. Sci. 14, 38 (2012)CrossRef
    29.N.J. Parmar, S.B. Teraiya, R.A. Patel, N.P. Talpada, Tetrahedron Lett. 52, 2853 (2011)CrossRef
    30.P. Prasanna, S. Perumal, J.C. Menendez, Green Chem. 15, 1292 (2013)CrossRef
    31.F. Lehmann, M. Holm, S. Laufer, J. Comb. Chem. 10, 364 (2008)CrossRef
    32.N.J. Parmar, H.A. Barad, B.R. Pansuriya, N.P. Talpada, RSC Adv. 3, 8064 (2013)CrossRef
    33.H. Mecadon, M. R. Rohman, M. Rajbangshi, B. Myrboh. Tetrahedron Lett. 52, 2523 (2011)CrossRef
    34.Litvinov YM, Shestopalov AA, Rodinovskaya LA, Shestopalov AM, J. Comb. Chem. 914 (2009)
    35.G. Vasuki, K. Kumaravel, Tetrahedron Lett. 49, 5636 (2008)CrossRef
    36.D. Shi, J. Mou, Q. Zhuang, L. Niu, N. Wu, X. Wang, Synth. Commun. 34, 4557 (2004)CrossRef
    37.T.S. Jin, A.Q. Wang, Z.L. Cheng, J.S. Zhang, T.S. Li, Synth. Commun. 35, 137 (2005)CrossRef
    38.Y. Peng, G. Song, R. Dou, Green Chem. 8, 573 (2006)CrossRef
    39.K. Kanagaraj, K. Pitchumani, Tetrahedron Lett. 51, 3312 (2010)CrossRef
    40.H.V. Chavan, S.B. Babar, R.U. Hoval, B.P. Bandgar, Bull. Korean Chem. Soc. 32, 3963 (2011)CrossRef
    41.S.R. Mandha, S. Siliveri, M. Alla, V.R. Bommena, M.R. Bommineni, S. Balasubramanian, Bioorg. Med. Chem. Lett. 22, 5272 (2012)CrossRef
    42.A. Siddekha, A. Nizam, M.A. Pasha, Spectrochim. Acta. A. 81, 431 (2011)CrossRef
    43.M. Bihani, P. P. Bora, G. Bez, J. Chem. 2013, 8 (2013). doi:10.​1155/​2013/​920719
    44.S. Gogoi, C.G. Zhao, Tetrahedron Lett. 50, 2252 (2009)CrossRef
  • 作者单位:Mohammad G. Dekamin (1)
    Mohammad Alikhani (1)
    Atefeh Emami (1)
    Hossein Ghafuri (1)
    Shahrzad Javanshir (1)

    1. Pharmaceutical and Heterocyclic Compounds Research Laboratory, Department of Chemistry, Iran University of Science and Technology, Tehran, 16846-13114, Iran
  • 刊物主题:Analytical Chemistry; Inorganic Chemistry; Physical Chemistry; Biochemistry, general; Organic Chemistry;
  • 出版者:Springer Berlin Heidelberg
  • ISSN:1735-2428
文摘
Dihydropyrano[2,3-c]pyrazole annulated heterocyclic compounds with diverse substituents on the 4H-pyran ring were efficiently prepared via a one-pot and four-component reaction of ethyl acetoacetate, hydrazine hydrate, aromatic aldehyde, and malononitrile. The procedure proceeds without utilization of any catalyst or solvent using ball milling technique at ambient temperature to afford desired medicinally important dihydropyrano[2,3-c]pyrazole derivatives. This protocol offers several advantages such as avoiding the use of any toxic and hazardous catalyst or solvent, mild reaction conditions, high to quantitative yields of products, low cost, and straightforward work-up.

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